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• W4386083911 abstract "Herein we report a practical crystallization-induced diastereomer transformation (CIDT) of oxime isomers for the scalable asymmetric synthesis of the bicyclic diamine (1S,6R)-3,9-diazabicyclo[4.2.1]nonane derivative that serves as a valuable building block in medicinal chemistry. The developed approach utilizes (S)-phenylethylamine as a chiral auxiliary handle for CIDT, and the starting nortropinone derivative is prepared in one step from commercially available materials. The resulting E-oxime is subjected to a stereospecific Beckmann rearrangement, followed by reduction of the resulting lactam with LiAlH4 to afford the monoprotected (1S,6R)-3,9-diazabicyclo[4.2.1]nonane derivative. The development of the CIDT and understanding of the mechanistic implications leading to the high selectivity are reported." @default.
• W4386083911 created "2023-08-24" @default.
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• W4386083911 date "2023-08-23" @default.
• W4386083911 modified "2023-09-26" @default.
• W4386083911 title "Development of a Crystallization-Induced Diastereomer Transformation of Oxime Isomers for the Asymmetric Synthesis of (1<i>S</i>,6<i>R</i>)-3,9-Diazabicyclo[4.2.1]nonane" @default.
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• W4386083911 doi "https://doi.org/10.1021/acs.joc.3c01228" @default.
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